4. Lee Murray
Lee Murray hasn’t fought professionally in 13 years. Considering he is currently serving a 25 year prison stretch in Morocco, it is probably fair to say his fight career is over.
Murray’s last bout was a decision loss to a 29-year old Anderson Silva for the Cage Rage middleweight championship. His previous bout before that had been his first and only ever fight in the UFC, a 1st round submission victory over Jorge Rivera at UFC 46.
In Murray’s childhood it is said that all the boys in his neighbourhood would fight regularly to establish a pecking order. He is also said to have once knocked out Tito Ortiz in a street-fight in 2002. While Tito denies this happened, Matt Hughes and Pat Miletich have both said they saw it happen.
Murray is currently in jail for his role in the Securitas Depot Robbery, a heist that netted £53,116,760 or $68,642,788.95 USD. Unfortunately for Lee they picked him up a few months later. He then had a prison escape attempt thwarted in June 2009. He’ll be well into his 60s by the time he’s released.